Chlorotrimethylsilane → 2,2,4,4,7,7-Hexamethyl-5-methylidene-3,6-dioxa-2,7-disilaoctane

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Reaction Steps

A solution of 1.6M n-butyllithium/n-hexane solution (100 ml) was dropwise added to a solution of diisopropylamine (22.4 ml) in dry tetrahydrofuran (50 ml) at -10° C., and the mixture was stirred for 1 hour. A solution of 3-hydroxy-3-methyl-2-butanone (8 ml) in dry tetrahydrofuran (50 ml) was dropwise added at -10° C. and the mixture was stirred for 1 hour. Then, trimethylchlorosilane (20.4 ml) was dropwise added at -10° C. After stirring at 4° C overnight, the reaction mixture was filtered with celite and the solid was washed with diethyl ether (500 ml). The combined filtrate was washed with 1N hydrochloric acid (150 ml×2) and a saturated aqueous solution of NaHCO3 (150 ml×2), and dried over MgSO4. The solvent was distilled away under reduced pressure. The residue was distilled under reduced pressure to give 16 g of the title compound (bp=85°-90° C./20 mmHg) as colorless liquid (see Table 2).

Provenance & Evidence